Preparation of certain 2‐ N ‐alkylamino‐and 2‐ N,N ‐dialkylamino‐10‐methylphenothiazines  via  phenothiazyne | Zendy

Biehl E. R. | Zendy; Patrizi V. | Zendy; Lapis S. | Zendy; Reeves P. C. | Zendy

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Preparation of certain 2‐ N ‐alkylamino‐and 2‐ N,N ‐dialkylamino‐10‐methylphenothiazines via phenothiazyne

Author(s) -

Biehl E. R.,

Patrizi V.,

Lapis S.,

Reeves P. C.

Publication year - 1974

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570110620

Subject(s) - chemistry , moiety , phenothiazine , acetonitrile , amine gas treating , lithium (medication) , solvent , medicinal chemistry , ammonia , organic chemistry , medicine , pharmacology , endocrinology

The treatment of 2‐chloro‐10‐methylphenothiazine, 1 , with lithium alkylamide/alkylamine or lithium dialkylamide/dialkylamine yields the corresponding 2‐ N ‐alkylamino‐or 2‐ N,N ‐dialkylaminophenothiazines in good yields via phenothiazyne. No significant reduction of 1 to 10‐methylphenothiazine is observed. Yields of amines obtained by this method are considerably higher than those obtained by reacting 1 with sodamide in refluxing amine solvent. Attempts to introduce the ‐CH 2 CN moiety onto the phenothiazine nucleus by treating 1 with sodamide and acetonitrile in liquid ammonia produced only 2‐amino‐10‐methylphenothiazine.

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